Born in Santander, Cantabria, Bolado made his professional debuts with hometown club Racing de Santander's first team in 2007–08, and scored three league goals during the season, one of them in the dying minutes of the final matchday, as Racing defeated CA Osasuna 1–0 at home, to secure a first ever UEFA Cup qualification. His La Liga debut came on 26 August 2007, in a 0–0 home draw against FC Barcelona.

In August 2008, Bolado was loaned for a season to second division outfit Elche CF, with a clause which permitted his return to Racing in the January transfer window if requested; he returned to the Cantabrians in June 2009, going on to spend the vast majority of 2009–10 in the sidelines, with a severe knee injury he sustained in pre-season.

In one of his first games upon his return to action, Bolado found the net twice - once through a bicycle kick - but Racing lost 3–4 at Athletic de Bilbao, on 29 March 2010.